Diamines in Catalysis and in Biological Systems

Currently there is a lot of interest in developing new methods for making chiral 1,2-diamines since they are building blocks not only for stereoselective catalysts, but also for a variety of therapeutic agents. Optically pure 1,2-diamines (or vicinal diamines) are used as organocatalysts in aldol condensation, Michael addition1-5 and Diels-Alder reactions or as metal ligands for stereoselective epoxidation, hydrogenation and dihydroxylation. In the realm of biology and biochemistry, diamine functionality is found in 1,2-diamino acids, β-lactam antibiotics and various pharmaceuticals. In chemotherapy, platinum 1,2-diamino complexes have long been used as antitumor agents. All these utilizations stimulated further research in the field of diamine synthesis. Numerous strategies have been developed to meet this need including coupling of bis-imines using low valent transition metals, preparation and subsequent reduction of diketones or addition of nitrogen sources to aziridine and epoxide moieties. This book describes novel methods which are more efficient and less cumbersome in preparation of chiral vicinal diamines.